


I Bet You Wouldn't...

by amethyst86



Category: Supernatural
Genre: M/M, Supernatural - Freeform
Language: English
Status: Completed
Published: 2015-02-06
Updated: 2015-02-06
Packaged: 2018-03-10 17:00:31
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,151
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3297761
Author URL: https://archiveofourown.org/users/amethyst86/pseuds/amethyst86
Summary: <blockquote class="userstuff">
              <p>Just a little one shot, mainly for the smut...</p><p>Boys will be boys... on a rare night off in new york, Sam, Cas and Dean enter into a game of Dares...</p>
            </blockquote>





	I Bet You Wouldn't...

"Ok, ok, ok, it's my turn!" Dean is jumping up and down in his seat like an excited toddler in a sweet shop. "I dare you, Sammy, to go over to that bloke over there, and ask him to kiss you!" Dean is laughing now, as he takes a long swig from his beer in front of him.

How did it come to this? It all started off innocently, team free will out on a piss up in New York. I guess this is what you get when you let three men out on their own in the big city on a night off from hunting. We had been to practically every bar and club along this street, and this street was a long one, we were all more than a little bit wasted. Two hours after we had originally set out, we had found ourselves in a club called "D.T.M." It was secluded from the rest of the clubs, almost hidden away. We walked down the flight of stairs, which nearly killed us, I don't know how many times Sam tripped and missed stairs. It was funny though.  
When we got into the main area of the club, our jaws his the floor.  
"Uhm, I think we're in a gay club..." I shake my head and take in my surroundings.  
"No shit, Cas!" Sam laughs, watching as two blokes practically mauled eachother in the corner of the room.  
"Oh well, gay clubs are the place to be!" Dean says happily, walking over towards the bar. Sam and I share a look, nod and follow Dean. Why not? We would only be here for half hour or so anyway, no big deal.  
Until it came to mine and Dean’s favourite drinking game of course. We just couldn't resist playing dares. We had found ourselves a little booth in the corner of the club and had gotten settled with one or four drinks and we let ourselves loosen up to our surroundings when Dean shouted suddenly; Sam. I bet you wouldn't...  
And that's how all this started, the dares started off normally, drink five shots straight down, do a shit dance in the middle of the dance floor. Perform a striptease on the podium. Now Dean had just dared Sam to do this.

"But what if he says yes?" Sam looks over at the man Dean is meaning, and shudders slightly.  
"Then do it! I wouldn't mess with that mans head, he looks like he could break your neck with one movement!" Dean smirks and watches the man who is knocking back a row of vodka shots.  
"But why him, why not... I don't know, that timid looking bloke over there?" Sam points over to a worm of a man stood hiding in a dark corner.  
"Because, that weedy guy hasn't been checking you out ever since you entered the room, goldilocks over there has!" Dean is laughing again now. "The forfeit will be even worse, Sammy!"  
Sam shakes his head slowly. "I can't do that... I... Jess..."  
"It's a night out, and she will never know, and besides, it's just a kiss. But if that is your refusal to do the dare, then I have a great forfeit, and if I utter the forfeit then you HAVE to do that, you can't turn a forfeit down!" Dean is nodding enthusiastically, he winks at me.  
Sam looks like the weight of a feather could knock him over as he stands up, and slowly walks over to ‘goldilocks’. Even from here I can see he is shaking. He's stood in front of the bloke now, and he is leaning in to talk in the man's ear. A few minutes later and the man nods, and Sam looks terrified as he leans forward again, and their lips meet.  
"Oh my God!" Dean is screeching in the chair next to me, his eyes glowing maliciously. "Oh my God, oh my God, oh my God! I didn't think he would actually do it!"  
I laugh but I don't take my eyes away from Sam and this man. Goldilocks is really enjoying this kiss, I can tell that simply by looking, he has one arm wrapped around Sam's waist, pulling him in close to him, the other arm is dangling around Sam's neck, his fingers stroking the flesh there.

Fifteen minutes later, and Sam is back, loaded with four beers that he places carefully on the table before he sits down.  
"Oh you shouldn't have!" Dean smiles and reaches out. Sam slaps his hand away.  
"I didn't, here you go Cas!" Sam hands me one of the beers and holds the other three close to him, and away from Dean. "It's to wash my mouth out after that... that..."  
Sam never finished his sentence. He shuddered violently before downing one of the pints before him.  
"He got an erection! He pulled me closer to him, and his dick was pressing into me!" Sam looks like he could throw up, but he downs another beer.  
"Dude..." Dean goes to talk, but Sam cuts him off.  
"Now, it's my turn!" Sam has a wry smile on his face, which is strange after what just happened. "I want you, to give Cas a blow job, in the middle of the dancefloor!" Sam smirked.  
"NO!" I yell out. "What he just dared you, I had nothing to do with it, I won't do it!"  
"But I've dared you!" Sam says simply, sipping at his third beer in five minutes.  
"It doesn't matter, you can't just..." I start, but again, Sam cuts in.  
"If you don't do it, then I get ultimate dare," Sam looks out at the dancefloor and looks away quickly. Goldilocks is eyeing him up as we speak.  
"You don't get ultimate dare, that's mine and Cas’, you don't get it!" Dean says quickly, his eyes dart over the table. Realising he doesn't have a drink, Dean nicks the beer Sam just bought me and knocks half of it back. He never was any good at downing drinks.  
"Fine, then I get to forfeit you, and the forfeit will only be worse," Sam nods, keeping his eyes looking down at the table.  
"Good, fine, forfeit!" Dean and I say at the same time, I take my drink back and down the other half.  
"The forfeit cannot be any worse than that!" Dean says, then looks at Sam, waiting.  
"Right, ok then, let’s go!" Sam knocks back the rest of his beer and stands up.  
I look at Dean, who is looking back at me. We both turn and face Sam. "Where are we going?"  
"To fulfil your forfeit, follow me!" Sam smirks and heads towards the exit.

"Sammy?" Goldilocks has stepped in front of Sam as he was about to ascend the stairs. Sam stops and just blinks at him. "I thought you were going to come over before you left?"  
"Er, I, jeez, sorry Gabe, I forgot I said that..." Sam stutters.  
"Well, that's ok, lucky I saw you leaving. Here..." Gabe leans in again and brings his lips to meet Sam's once more. I notice Sam's whole body tense up as Gabe pulls himself right up into Sam's space, his arms wrapped around his neck. Correction, his left arm is straying down Sam's back, stroking along his shirt and resting on his ass. Gabe slips a piece of paper into the back pocket there.  
"Dude, I just saw tongues!" Dean is hopping on the spot, laughing quietly.  
"I know, it would appear he is returning the favour!" I laugh. It was true, Sam appeared to be giving as much to this kiss as he was receiving, the only difference was, Sam's body was still tense, whereas Gabe was totally relaxed. I flicked my eyes down to where Gabe's hand was resting on Sam's ass, and noticed that Sam was signalling with his own hands. Although there was no obvious meaning to this signal, I guessed that it was a 'save me' tactic, so I interrupted.  
"Er, Sam, we've got to go, the cab's here!" I smile politely as Gabe stops sucking at Sam's face. Gabe nods at Sam and smiles. "Call me!" He walks off, swaggering his ass.  
Dean is still creased over with silent laughter.  
"Come on!" Sam is definitely not in a good mood now as he literally runs up the stairs and out of the club. I jog up behind him, and Dean follows. Sam is already at the curb side, hailing a taxi by the time me and Dean get outside.

Sam has directed the taxi back to our motel. Although he has a small smile on his face, I can tell that he is still in an awful mood. I feel it's best not to talk to him and the journey back is in complete silence.  
"That's twenty-six dollars!" The driver says as he pulls up outside the motel, he's looking at Sam. Sam just blinks at him. I can't help but laugh. In the end, Dean pulls his wallet out and pays, whilst me and Sam clamber out drunkenly. Dean follows a couple of minutes later.

Inside the motel, Sam leads us back up to the floor where our rooms are, he stops outside of Dean's.  
"You both go in there, I'll be back in a minute," Sam is slurring now, I'm guessing those last three beers knocked him for six. He walks up the corridor a few doors, until he is stood outside Bobby's room, he knocks loudly.  
"Bobby isn't going to like that!" Dean says, as he unlocks his door and walks into his room. I peer through the door before entering and laugh.  
"Dean, you’ve had this room a day and your stuff is everywhere!’ I walk further into the room and pick up a pair of boxers that have managed to get caught onto the antenna of the T.V.  
"Dude, don't touch my underwear," Dean blinks at me seriously, and I drop them to the floor. "Thank you!" Dean walks over and picks them back up, he puts them back onto the antenna. "I'll be able to find them when I pack now!"  
‘Yes!" I smirk and look around the room. "I don't think housekeeping even bother with your room. I don't actually blame them." Just as I finished my sentence, the door knocks, and Dean lets a smiley Sam into the room.  
"Did Bobby not kill you for waking him up at an ungodly hour?" Dean raises his eyebrow.  
"It's only one, Dean, he was still up arranging stuff for us tomorrow!" Sam says, he has a video recorder in his hand.  
"What's that?" I ask dumbly.  
"A video recorder!" Sam says slowly, as though he was talking to a three-year-old. He puts it on the bed and disappears back out into the corridor. He wanders back in a few seconds later with a tripod under his arm. He starts to set it all up.  
"What's it for?" Dean is watching Sam as he works.  
"For your porn video!" Sam says, casual as you like, so casual in fact, that he could have just said, "To record playdays!"  
"Er, my, um... what?" Dean looks confused.  
"It's your forfeit, you cannot turn it down! You, and Cas over there, are going to record... a porn video. There!" Sam stands up straight and rubs his hand together. "All set, all we need now, is for the actors to do their bit! I won't stay. Not actually something I want to witness, but, I will get someone to scan the video to make sure it is you two, and that you have done what the forfeit asks! Goodnight!" Sam smirks as he walks out of the room, leaving me and Dean alone. With a camcorder.  
"Dude..."  
"Shut up!"

Twenty minutes later, and we are stood in exactly the same places as we were before. Dean is eyeing the video camera up, I am just thinking, "No, no, no!"  
"What can he really do, if we don't do this?" Dean asks, perching himself on the edge of his bed.  
"I don't know, I... he could come up with something worse maybe?"  
"What could be worse than this?" Dean screeches.  
"I'm not that bad," I try to lighten the mood. Dean didn't find it very funny though. "Look, right, he might come up with something like. I don't know, he could take us back to that club, and say we had to do a porno with one of them gay men, and well, we don't know where they've been, and they are going to be less inclined to say no to all of this. Especially when it concerns two good looking men like us!" Dean snorts.  
"Would you rather do this now, here, in private, with someone you have known for years, or with a complete stranger who Sam paired you up with in a gay bar?" I ask, sitting on the opposite end of the bed.  
"When you put it that way... No, I'd prefer not to do it at all!" Dean says sulkily, he actually stamps his foot.  
"Well, we don't have that choice, so... um, I guess we should..." I don't really know how to finish the sentence, so I just pull my shirt over my head to make my point. Dean is just gawping at me.  
"Who's going to do... you know, who's going to do what?" Dean is following suit now, he pulls his shirt off, and starts to unbutton his trousers. I unbuckle my belt as I think of an answer for Dean.  
"Right, so we could, hmmm, I'll you know, and then you can, Erm, well, you know?" Is the best I can come up with.  
"I think we should just, see what happens, maybe," Dean half laughs as he wiggles out of his trousers and pulls his socks off. We are both stood in just our boxers, looking at each other. I shake my head and walk over to the camcorder. "Get on to bed, I'll make sure it's filming the right place!" Dean blushes as he climbs onto the bed. He lays down in the middle of the bed, his head stays off of the bed, watching me.  
"That's it, it's in the right place, how do I rec... never mind, got it!" I press the red record button, and step out from behind the camera. Dean shuffles on the bed.  
"Don't move! It's in the right place, I'll just um, come over to you!" I say quickly, I step closer to the bed and sit down. "Ok, this is it, we just, just imagine I'm Lisa!"  
"That's going to be a little hard, Cas!" Dean retorts.  
"Well, just try!" I snap, as I slide up the bed and lay next to Dean. I lay on my side facing Dean, and he stares back, almost innocently at me.  
This is it. No going back now.

I put my hand out, running it along Dean’s cheek, hoping to reassure him, before we get into this properly. Then I run it lower, under his chin, across his torso and along his belly. I smile at him, then lean my head in. Slowly, I put my mouth to his, and we start an unsure kiss. I allow my hand to run along the rim of his boxers, then I slide my hand under the material, I put my hands around the back of him and squeeze his ass. The kiss deepens, and Dean slides his tongue into my mouth and pulls his body in closer to my own.  
I push him onto his back, my mouth still on his. I lean on my elbows and steady myself on top of him. I thrust my own tongue into Dean’s mouth and I position my leg between his. I nudge his legs open slightly, and lightly rub my thigh against his dick. Dean groans into my mouth. He brings his arms up and around my neck, he allows his fingers to stroke along my back, and down further, he pulls my boxers down slightly over my waist and brings his left arm from behind my back, and he starts to stroke up and down the length of my dick. I sigh into his mouth this time, as I feel my dick start to harden under his touch. I slide myself down Dean's body, my lips leaving his, and instead making contact with his neck, then lower towards his chest. I flick my tongue out around his nipples and feel them harden into little bumps under my tongue. I trail my tongue down his stomach, past his belly button, until I reach the restriction that is Dean’s boxers. I pull them down swiftly, so they are level with his knees, then take in the sight that is Dean’s dick. He’s hard, really hard. I eye up the thick blue vein throbbing and flick out my tongue to lick the underneath of Dean’s dick, I work from the base to his head, then I put my whole mouth over the head, I drop down, taking in as much of Dean as I can without gagging. Dean is moaning louder now, he bucks his hips up and forces his dick deeper into my throat. The saltiness of pre-cum hits my taste buds. I twist my tongue around the base of his dick, as I lift my head back up, and then engulf the length of Dean, again and again. His breathing is manic now, and I know myself how this feels. I know that Dean is close to the edge now, so I pull my head back, just in time for Dean to explode his load into the back of my throat. Reflex forced me to swallow the fluid, as I carried on sucking at his dick to ride out his orgasm. His body is fully relaxed now, as I slide myself back up, so I am level with him. A dull smile is on his lips, and he looks up at me, from where he lays. His hair is stuck to his forehead with sweat, he has a tint of red in his complexion, it's the first time I've seen Dean this laid back. Dean’s job is a tough one, and comes with a fair amount of stresses, it’s nice to see him so relaxed. I smile down at him, then rock his shoulder, hinting at him to sit up. I'm not finished yet.  
Dean doesn't do as requested. Instead, he pulls me down, and he straddles me. He looks down at me, and I see something flash across his face, before I can catch the emotion, Dean jumps off me and heads to the bathroom. Shit.  
I sit up, thinking how we to apologise for this, this… whatever this is… but then Dean is back, with a glint in is eye, and a tub of Vaseline in his hand.  
Shit.  
The devilish look in Dean’s eyes spur me on though, and when he climbs back onto the bed, I make sure I’m in control. I flip him back onto his back, and take the Vaseline from him, twisting the lid off and dipping two fingers into the goo.  
I place my legs between Dean’s once more, and spread him wide, then move my fingers to his hole, and circle them there.  
Dean gasps, and there’s definitely a look of worry behind his eyes, but it’s mixed with excitement.  
“Don’t worry, I’ve got you,’ I whisper, and slowly I breach his hole with one finger. Dean grips my hips tight, tight enough to bruise as I move my finger in and out, before adding a second.  
“Oh God,” Dean moans loudly as I start to scissor my fingers inside him. “Oh. My. Fucking God. Cas I need this,” Dean practically shouts this time, and I feel Dean’s dick pressing against my stomach between us. He’s hard again already!  
“I, erm, I mean… are you sure?!’ I ask, and in reply, Dean grabs my face down to his and kisses me hard.  
I grab the Vaseline again and run my hand up and down my own length, hoping I’ve used enough to make this as painless as possible for Dean. This is new to both of us.  
I put my hands under Dean’s knees, and lift his legs over my shoulders. I look down at Dean, and his green eyes are filled with lust and want.  
“Come the fuck on Cas,” he grunts, trying to wiggle his ass closer to me.  
I needed no more encouragement. I line up my cock with Dean’s opening, and slide slowly in. Inch by glorious inch. My eyes don’t leave Dean’s. His eyes are closed and his face is a mix of emotions and he holds me still for a few minutes. After some time, he flickers his eyes open, and in a thick voice he whispers, ‘Move Cas.’  
Gently at first, I pull back out of Dean, leaving only the head of my dick buried in Dean’s tight hole, and then slowly I sink back into him.  
‘God damnit Cas, harder,’ Dean grunts, his face twisting, and his hands still digging bruises into my skin. I pull back out, but this time, I slam back into him. I start up a steady pace and our bodies work together to create a rhythm that works. I close my eyes and slam back into Dean, my balls slapping against his ass. Over and over. The wet sound only adding to my pleasure with every ‘thwack’.  
After mere minutes, I feel that familiar tug in the pit of my stomach, and feel my dick stiffen even more inside of Dean, who groans in response.  
As my orgasm grows, Dean grabs his own dick and starts pumping himself. And I’ve never seen anything so hot in all my life. My orgasm erupts at the same time as Dean brings himself to orgasm. I thrust into Dean a couple more times to ride out my orgasm, then slip out of him and roll to his side.  
We lay side by side for mere seconds before Dean jumps up and switches the camcorder off.  
"Wow!" I say finally, getting up from the bed and locating my boxer shorts.  
"Is it wrong that I kind of, well... enjoyed that?" Dean asked, whilst he pulled his jeans on.  
"I hope not, because I did too!" I say honestly, walking into the bathroom.  
"Good! Not that I'm, you know, gay!" Dean mumbles.  
I laugh out loud in the bathroom as I splash warm water across my stomach to get rid of the trail of Dean's sperm. "I know Dean!"  
"And you won't tell Lisa?"  
"Why would I do that? Anyway, we now have dibs on Sam! It's our turn!" I say, walking back into the bedroom, I find my t-shirt and pull it over my head.  
"I don't think we could come up with anything worse than, I mean, anything as good as, I don't think we could come up with anything like that!" Dean stumbles over his words.  
"Trust me, I think we can!" I pull out a piece of paper from the pocket of my jeans, that were still strewn across the floor. "I nicked this from Sam in the taxi!" I hand the paper over to Dean.  
"Ha, ok, I'll go and get Sammy, you call!" Dean ran out of the bedroom excitedly.  
I pulled my jeans on and grabbed my mobile. I dialled in the number and listened to the ringing at the other end of the phone.

"What the fuck do you want? I was sleeping!" Sam has just entered the bedroom, with Dean following not far behind. "How did your porno go?" Sam grins when he spots the camera.  
Someone answers the phone on the other end. "Yeah?"  
"Hello, Gabe...? This is Sammy, I was just wondering if you were up to coming to my motel room tonight... I'm feeling a bit lonely... I like to make videos, are you free?... You are... great! Room 125 at the Jane Hotel... yes that's the one... great, see you in ten!" I hang up the phone and grin at Sam.  
"It's our turn! You are going to do exactly what me and Dean just have, and it will be recorded on the end of that video tape. There's a good hour left on that tape, use it all up!" Dean laughed. "Meanwhile, I'm going to crash in Cas' room, because, watching you and Gabe make out is not something I want to see! Coming Cas?"  
I just nod, smirking at Sam. "If you don't do it, the forfeit is, you have to… there is no forfeit… you have to do it!" With that, me and Dean walk out of the room, laughing at Sam’s expense.


End file.
